1,3-苯并噻唑-5-基乙酸酯 | 58249-68-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 中文名称: 1,3-苯并噻唑-5-基乙酸酯
• 英文名称: 5-Acetoxybenzothiazol
• 英文别名: 5-acetoxy-benzothiazole；1,3-Benzothiazol-5-yl acetate
• CAS: 58249-68-6
• 化学式: C₉H₇NO₂S
• 分子量: 193.226
• InChiKey: ZGXJCIUFKKUQQV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  67.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,3-苯并噻唑-5-基乙酸酯 在 [RuCl(P(C₆H₅)3)2(O(C₆H₄)NCH(C₄H₃N))] 、 bromamine B 、 sodium hydroxide 作用下， 以 水 、 乙腈 为溶剂， 反应 4.67h， 以95%的产率得到4-acetyloxy-2-aminobenzenesulfonic acid
  参考文献：
  名称：

  Development of an efficient ruthenium catalyzed synthetic process and mechanism for the facile conversion of benzothiazoles to orthanilic acids

  摘要：

  Ruthenium-Schiff base complex catalyzed efficient protocol has been developed for the synthesis of orthanilic acids from benzothiazoles in good to excellent yields using N-haloamines. Hexa-coordinated ruthenium complex with Schiff base and triphenylphosphine ligands has been prepared and its catalytic function was invented for the synthesis of orthanilic acids. The synthetic process utilizes our efficient method for the selective and preferential oxidation of thiazole ring of benzothiazoles using N-haloamines without effecting phenyl ring. The detailed catalytic, mechanistic and kinetic investigations have been made for the synthetic reactions. Solvent isotope studies have been made in H2O-D2O and the reactions were carried out at different temperatures. Under the identical set of conditions, the kinetics of catalyzed reactions has been compared with uncatalyzed reactions and found that the catalyzed reactions are 9-11 folds faster. The catalytic constants (K-c) have been calculated for each N-haloamine at different temperatures and the values of activation parameters with respect to the catalyst have been evaluated. Spectroscopic evidence for the formation of 1:1 complex between N-haloamine and ruthenium has been obtained. The observed results have been explained by a plausible mechanism and the related rate law has been deduced. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2010.06.006
• 作为产物：
  描述：

  1,3-benzothiazole-5-diazonium;tetrafluoroborate 、 溶剂黄146 以32%的产率得到
  参考文献：
  名称：

  MCKILLOP A.; SAYER T. S. B.; BELLINGER G. C. A., J. ORG. CHEM. , 1976, 41, NO 8, 1328-1331

  摘要：

  DOI：

文献信息

• The Efficient Palladium-Catalyzed Selective t Synthesis of Benzenesulfonic Acids
  作者：Rajenahally V. Jagadeesh、Y. Sree Sandhya、P. Karthikeyan、S. Sudhakar Reddy、P. Pradeep Kumar Reddy、M. Viniod Kumar、K. T. Prabhu Charan、R. Narender、P. R. Bhagat

  DOI：10.1080/00397911.2010.502991

  日期：2011.8.15

  [image omitted] Palladium-catalyzed synthetic methodology has been developed for the synthesis of 2-aminobenzenesulfonic acids from benzothiazoles in good to excellent yields using chloramine-B in alkaline (pH 12) acetonitrile/water (1:1) at 80 degrees C.
• Reaction of benzothiazole and substituted benzothiazoles with dimethyl acetylenedicarboxylate. A novel heterocyclic ring transformation
  作者：Alexander McKillop、Trevor S. B. Sayer、Geoffrey C. A. Bellinger

  DOI：10.1021/jo00870a007

  日期：1976.4